Farnesyl diphosphate

Manufactured by Merck Group

Sourced in United States

Farnesyl diphosphate is a key intermediate in the biosynthesis of various isoprenoid compounds, including sterols, dolichols, and prenylated proteins. It serves as a substrate for various enzymes involved in these metabolic pathways.

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Farnesyl diphosphate (FPP), (2 citations)

8 protocols using farnesyl diphosphate

Elucidating Isoprenoid Biosynthesis Pathway

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Isopentenyl diphosphate (IDP), dimethylallyl diphosphate (DMADP), geranyl diphosphate (GDP), farnesyl diphosphate (FDP), geranylgeranyl diphosphate (GGDP), 1,9-decadiene, ammonium bicarbonate, chlorogenic acid, formic acid, tert-butyl methyl ether (TBME), methanol and acetonitrile (LC-MS grade) were purchased from Sigma-Aldrich (St. Louis, MO, United States). Trimethylsulfonium hydroxide (TMSH) was ordered from Macherey-Nagel (Düren, Germany).

Nagel R., Hammerbacher A., Kunert G., Phillips M.A., Gershenzon J, & Schmidt A. (2022). Bark Beetle Attack History Does Not Influence the Induction of Terpene and Phenolic Defenses in Mature Norway Spruce (Picea abies) Trees by the Bark Beetle-Associated Fungus Endoconidiophora polonica. Frontiers in Plant Science, 13, 892907.

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Isoprenoid Biosynthesis Precursor Compounds

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All-trans-farnesol, all-trans-geranylgeraniol, farnesyl diphosphate, geranylgeranyl diphosphate, dexamethasone, fosmidomycin, methyl-jasmonate, ethephon and mevalonolactone were purchased from Sigma-Aldrich (Saint Quentin Fallavier, France). Cellulase RS was obtained from Yakult Pharmaceutical Industry (Tokyo, Japan), and mevinolin was a kind gift from Drs. M. Greenspan and A.W. Alberts (Merck Sharp and Dohme, Rahway, NJ, USA). Before use, the lactone forms of mevinolin and mevalonolactone were converted into their free salt forms, as described by [28 (link)]. 1-deoxy-d-xylulose (DX) was obtained from AlsaChim (Illkirch Graffenstaden, France). (R,S)-[2-¹⁴C]mevalonolactone was purchased from Amersham. Analytical-grade solvents were purchased from Sigma-Aldrich (Saint Quentin Fallavier, France), Carlo Erba (Val-de-Reuil, France), or Fischer Scientific France (Illkirch-Graffenstaden).

Chevalier Q., Huchelmann A., Debié P., Mercier P., Hartmann M., Vonthron-Sénécheau C., Bach T.J., Schaller H, & Hemmerlin A. (2024). Methyl-Jasmonate Functions as a Molecular Switch Promoting Cross-Talk between Pathways for the Biosynthesis of Isoprenoid Backbones Used to Modify Proteins in Plants. Plants, 13(8), 1110.

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Characterization of Isoprenoid Precursors

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Unlabeled isopentenyl diphosphate, dimethylallyl diphosphate, geranyl diphosphate, farnesyl diphosphate, geraniol, farnesol and geranylgeraniol were purchased from Sigma-Aldrich (Sigma-Aldrich, St. Louis, MO, USA). All other chemicals were of analytical grade.

Wang Y., Zhang N., Yan J., Li C., Zeng N., Wang D., Li Z., Li B, & An Y. (2024). The Property of a Key Amino Acid Determines the Function of Farnesyl Pyrophosphate Synthase in Sporobolomyces pararoseus NGR. Current Issues in Molecular Biology, 46(4), 3108-3121.

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Characterization of terpene synthases

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Standards used include: trans-nerolidol (Sigma-Aldrich, 04610590), farnesol (Sigma-Aldrich, F203), linalool (Aldrich, L2602). All C₁₆ compounds isolated from yeast cultures and characterized by NMR were used as in-house standards. Substrates used for in vitro reactions of recombinant SpSodMT wt protein with SAM (A2408-Sigma) and geranyl diphosphate (G6772; Sigma-Aldrich), farnesyl diphosphate (F6892; Sigma-Aldrich), and geranylgeranyl diphosphate (G6025; Sigma-Aldrich). Phusion High-Fidelity DNA Polymerase (New England BioLabs, M0530S) and MyTaq DNA polymerase (BIO-21105, Bioline) were used in PCR amplifications. QIAquick Gel Extraction Kit (#28704, Qiagen) was used for gel extraction and DNA purification. NucleoSpin Plasmid Kit (740588.250, Macherey-Nagel) was used for plasmid DNA purification.

Ignea C., Raadam M.H., Koutsaviti A., Zhao Y., Duan Y.T., Harizani M., Miettinen K., Georgantea P., Rosenfeldt M., Viejo-Ledesma S.E., Petersen M.A., Bredie W.L., Staerk D., Roussis V., Ioannou E, & Kampranis S.C. (2022). Expanding the terpene biosynthetic code with non-canonical 16 carbon atom building blocks. Nature Communications, 13, 5188.

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Isoprenoid Precursor Synthesis

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Isopentenyl pyrophosphate (IPP), dimethylallyl pyrophosphate (DMAPP), geranyl diphosphate (GDP), farnesyl diphosphate (FDP), and geranylgeranyl diphosphate (GGDP) were purchased from Sigma–Aldrich.

Chai H., Yin R., Liu Y., Meng H., Zhou X., Zhou G., Bi X., Yang X., Zhu T., Zhu W., Deng Z, & Hong K. (2016). Sesterterpene ophiobolin biosynthesis involving multiple gene clusters in Aspergillus ustus. Scientific Reports, 6, 27181.

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Purification of E. coli BL21 AI Protein

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Escherichia coli BL21 AI cells were acquired from Thermo Fisher Scientific (Waltham, MA, USA). Farnesyl diphosphate (FPP) and N-lauroylsarcosine sodium salt (NLS) were purchased from Sigma-Aldrich (St. Louis, MO, USA), while homogentisate (HGA) was obtained from TCI (Shanghai, China). DMC was synthesized as described previously (Ikishima 2010 ).
For detergent screening, we used N-dodecyl-β-D-maltopyranoside (DDM), N-dodecyl phosphocholine (DPC), n-decyl-N,N-dimethylglycine (DDGly), n-nonyl-β-D-maltopyranoside (NM), n-dodecyl-N,N-dimethylamine-N-oxide (LDAO), glyco-diosgenin (GDN), and lauryl maltose neopentyl glycol (LMNG), all purchased from Anatrace (Maumee, OH, USA).
For purification, we used Ni²⁺-NTA resins from QIAGEN (Duesseldorf, Germany) and Superdex 200 10/300 GL column from GE Healthcare (Little Chalfont, Buckinghamshire, UK).

Xiao H., Mei L.C., Lin H.Y., Chen Z., Yu X.H., Yang J., Tong Q, & Yang G.F. (2024). Expression, purification, and characterization of transmembrane protein homogentisate solanesyltransferase. Applied Microbiology and Biotechnology, 108(1), 256.

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Analysis of Volatile Compounds in Tea

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Five-year-old tea plants of Camellia sinensis cv. “Shu Cha Zao” grown at the experimental farm of Anhui Agricultural University in Hefei, China, were used in this study. Standards of geranyl diphosphate (GDP), farnesyl diphosphate (FDP), β-myrcene, β-ocimene, linalool, geraniol, α-citral, β-citral, methyl geranate, nerol, D-limonene, trans-linalool oxide (furanoid), neryl acetate, L-terpineol, α-terpinen, geranyl acetone, thymol, (Z)-nerolidol, α-farnesene, β-farnesene, (E)-nerolidol, humulene, α-ionone, β-ionone, (E)-γ-bisabolene, cadinol and caryophyllene were purchased from Sigma-Aldrich (St. Louis, MO, USA).

Jin J., Zhang S., Zhao M., Jing T., Zhang N., Wang J., Wu B, & Song C. (2020). Scenarios of Genes-to-Terpenoids Network Led to the Identification of a Novel α/β-Farnesene/β-Ocimene Synthase in Camellia sinensis. International Journal of Molecular Sciences, 21(2), 655.

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Characterization of Prenyltransferase Enzymes

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For the characterization of the prenyltransferases 200 µl enzymatic assays were carried out in glass vials. The reaction mixture contained 10 mM MOPS buffer (pH 7.0), 5 mM MgCl 2 , 1 mM DTT, 1 mg/ml BSA, 100 µΜ prenyl diphosphate substrate. The substrates used were: dimethylallyl pyrophosphate (D4287, Sigma-Aldrich), isopentenyl diphosphate (I0503, Sigma-Aldrich), geranyl diphosphate (G6772, Sigma-Aldrich), farnesyl diphosphate (F6892, Sigma-Aldrich), geranylgeranyl diphosphate (G6025, Sigma-Aldrich). The reactions were initiated by addition of 50 ng of purified enzyme. After 16 h incubation at 25 °C, the reactions were terminated by addition of equal volume of 2N HCl in 83% EtOH and after 20 min incubation they were neutralized with 0.14 mL of 10% NaOH.
The hydrolyzed diphosphates were extracted three times using 300 µl of hexane. The hexane extracts were concentrated to a final volume of 50 µl and 1 µl of each reaction was used for GC-MS analysis (Methods S1). Individual compounds were identified by comparing their GC retention indices and mass spectra with those of authentic standards.

Athanasakoglou A., Grypioti E., Michailidou S., Ignea C., Makris A.M., Kalantidis K., Massé G., Argiriou A., Verret F, & Kampranis S.C. (2019). Isoprenoid biosynthesis in the diatom Haslea ostrearia. The New phytologist, 222(1).

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